Sodium hydride → HCID 53770837、化合物

HRID 488154

反応式

HRID 488154 の反応式
[O:1]=[C:2]([CH3:10])[CH2:3][P:4](=[O:9])([O:7][CH3:8])[O:5][CH3:6].[H-].[Na+].[CH2:13](Br)[CH:14]=[C:15]([CH2:17][CH2:18][CH:19]=[C:20]([CH2:22][CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])[CH3:21])[CH3:16]>C1COCC1>[C:2]([CH:3]([P:4](=[O:9])([O:7][CH3:8])[O:5][CH3:6])[CH2:13][CH:14]=[C:15]([CH3:16])[CH2:17][CH2:18][CH:19]=[C:20]([CH3:21])[CH2:22][CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])(=[O:1])[CH3:10]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 77872Dimethyl (2-oxopropyl)phosphonateHCID 550199Farnesyl bromide

生成物 1

HCID 53770837HCID 53770837、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
20 °C

実験手順

Dimethyl 2-oxopropylphosphonate (560 μL, 4.0 mmol) was added dropwise to a stirred suspension of sodium hydride (50% oil suspension, prewashed with hexane) (210 mg, 4.8 mmol) in anhydrous THF (15 mL) at 20° C. under an Argon atmosphere. The resulting slurry was stirred at 20° C. for 2 hours to allow for complete formation of the sodio derivative and then treated dropwise with farnesyl bromide (1.14 mL, 4.2 mmol). The cloudy yellow mixture was stirred at 20° C. for 2 hours and then quenched with saturated NH4Cl solution. The resulting mixture was washed with water, dried, filtered and evaporated to give the crude product which was purified by flash chromatography on a silica gel column. Elution of the column with hexane:ethyl acetate:methanol (40:10:1, v:v:v) gave the title compound as gum.

後処理

  1. stirringThe cloudy yellow mixture was stirred at 20° C. for 2 hours
  2. customquenched with saturated NH4Cl solution
  3. washThe resulting mixture was washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customto give the crude product which
  8. customwas purified by flash chromatography on a silica gel column
  9. washElution of the column with hexane:ethyl acetate:methanol (40:10:1, v:v:v)

出典と根拠

ORDレコード
ord-37315ade40574a3dab8693161682355a
出典データセット
uspto-grants-1994_03
特許番号
US05298655

関連ノート

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